Windsor Vacation Rentals

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Our top choices for Windsor vacation rentals

Windsor Home with Sauna & Outdoor Fire Pit

Windsor Home with Sauna & Outdoor Fire Pit
Windsor
$770 nightly
The price is $868
Mar 30 - Mar 31
Total with taxes and fees
Windsor Home with Sauna & Outdoor Fire Pit

TOP HOST - Vacation Memories Just Waiting to be Made - 2 Bedroom - Sleeps 6

TOP HOST - Vacation Memories Just Waiting to be Made - 2 Bedroom - Sleeps 6
Windsor
$399 nightly
The price is $441
Mar 29 - Mar 30
Total with taxes and fees
TOP HOST - Vacation Memories Just Waiting to be Made - 2 Bedroom - Sleeps 6

Elegant Vineyard Living at a Private Wine Country Estate

Elegant Vineyard Living at a Private Wine Country Estate
Windsor
8.4 out of 10, Very Good, (6 reviews)
"What an amazing place! The hosts made it very easy to be prepared for our stay."
United States
Eric B.
$928 nightly
The price is $1,043
Mar 29 - Mar 30
Total with taxes and fees
Elegant Vineyard Living at a Private Wine Country Estate

Top Wine Country Condo - Full Resort Amenity Access - 2 Bedroom/2 Bath - Sleep 6

Top Wine Country Condo - Full Resort Amenity Access - 2 Bedroom/2 Bath - Sleep 6
Windsor
$399 nightly
The price is $441
Mar 29 - Mar 30
Total with taxes and fees
Top Wine Country Condo - Full Resort Amenity Access - 2 Bedroom/2 Bath - Sleep 6

One Click Away from Vacay - Full Resort Access - 2 Bedroom / 2 Bath - Sleep 6

One Click Away from Vacay - Full Resort Access - 2 Bedroom / 2 Bath - Sleep 6
Windsor
$399 nightly
The price is $441
Mar 29 - Mar 30
Total with taxes and fees
One Click Away from Vacay - Full Resort Access - 2 Bedroom / 2 Bath - Sleep 6

Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6

Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
Windsor
9.2 out of 10, Wonderful, (44 reviews)
"Check-in was a little difficult, but the condo itself was convenient and a great stay."
United States
SB L.
$337 nightly
The price is $373
Mar 30 - Mar 31
Total with taxes and fees
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6

Creekside Under the Redwoods

Creekside Under the Redwoods
Guerneville
9.8 out of 10, Exceptional, (18 reviews)
"Very cute and comfortable place! We enjoyed our stay!"
United States
Kathy M.
$280 nightly
The price is $311
Mar 30 - Mar 31
Total with taxes and fees
Creekside Under the Redwoods

Tranquil Redwood Retreat

Tranquil Redwood Retreat
Guerneville
8.8 out of 10, Excellent, (10 reviews)
"Perfect hun for enjoying downtown guernville "
United States
Alex A.
$290 nightly
The price is $321
Mar 29 - Mar 30
Total with taxes and fees
Tranquil Redwood Retreat

Backyard Garden Oasis

Backyard Garden Oasis
3.0 star property
Middletown
9.6 out of 10, Exceptional, (51 reviews)
"Cute garden area, quiet, nice all inclusive spot"
United States
Jodi
$209 nightly
The price is $233
Mar 27 - Mar 28
Total with taxes and fees
Backyard Garden Oasis

Russian River Retreat! Woodsy Guerneville Bungalow

Russian River Retreat! Woodsy Guerneville Bungalow
3.0 star property
Guerneville
$382 nightly
The price is $432
Mar 30 - Mar 31
Total with taxes and fees
Russian River Retreat! Woodsy Guerneville Bungalow

Mandala Springs Wellness Retreat Center

Mandala Springs Wellness Retreat Center
3.5 star property
Cobb
8.8 out of 10, Excellent, (30 reviews)
"Very clean room, friendly staff, great to walk around "
United States
Victoria
$125 nightly
The price is $140
Mar 29 - Mar 30
Total with taxes and fees
Mandala Springs Wellness Retreat Center

Rouge Cobb Mountain Hotel - Cabin 1

Rouge Cobb Mountain Hotel - Cabin 1
2.0 star property
Cobb
$225 nightly
The price is $251
Apr 1 - Apr 2
Total with taxes and fees
Rouge Cobb Mountain Hotel - Cabin 1

Sundog Cottage - Clean & Cozy - EV - Walk to Food & Beach - Fenced Yard for Dog

Sundog Cottage - Clean & Cozy - EV - Walk to Food & Beach - Fenced Yard for Dog
Dillon Beach
10.0 out of 10, Exceptional, (70 reviews)
"We had a great stay at Sundog cottage! Very clean and comfortable. Easy walk to the beach!"
United States
Donna H.
$531 nightly
The price is $597
Mar 29 - Mar 30
Total with taxes and fees
Sundog Cottage - Clean & Cozy - EV - Walk to Food & Beach - Fenced Yard for Dog

Winemaker's Delight: 3BD/3BA Russian River Valley

Winemaker's Delight: 3BD/3BA Russian River Valley
Northwest Santa Rosa
9.8 out of 10, Exceptional, (72 reviews)
"Loved our stay!!"
United States
kristen s.
$449 nightly
The price is $505
Mar 29 - Mar 30
Total with taxes and fees
Winemaker's Delight: 3BD/3BA Russian River Valley

Escape to Wine Country in your independant Cottage in Downtown Calistoga

Escape to Wine Country in your independant Cottage in Downtown Calistoga
Calistoga
10.0 out of 10, Exceptional, (2 reviews)
"Loved everything Ellen was very accommodating ,pleasant and polite As well as professional The furnishings were very up scale and same style as my home One suggestion The tv should be more accessible so it does not block AC when pulled out from the wall I’m not being critical because I love this place. I will stay there every time I would ever be close to Calistoga. AND I adore Ellen personally and professionally!!👍❤️"
United States
Ronny
$319 nightly
The price is $383
Mar 30 - Mar 31
Total with taxes and fees
Escape to Wine Country in your independant Cottage in Downtown Calistoga

Glen Ellen Retreat #3 King Beds

Glen Ellen Retreat #3 King Beds
Glen Ellen
10.0 out of 10, Exceptional, (75 reviews)
"Perfect for a weekend getaway with family."
United States
Tara C.
$469 nightly
The price is $518
Mar 30 - Mar 31
Total with taxes and fees
Glen Ellen Retreat #3 King Beds

Peaceful, charming, cottage in wine country. Beautiful yard!

Peaceful, charming, cottage in wine country. Beautiful yard!
Sebastopol
10.0 out of 10, Exceptional, (11 reviews)
"Great stay and location!"
United States
Brandi K.
$310 nightly
The price is $343
Mar 31 - Apr 1
Total with taxes and fees
Peaceful, charming, cottage in wine country. Beautiful yard!

Escape to wine country in your independent cottage in downtown Calistoga

Escape to wine country in your independent cottage in downtown Calistoga
Calistoga
10.0 out of 10, Exceptional, (3 reviews)
"We made the Calistoga CA area our base for our recent trip and the Cottage Grove Inn served as a great place to stay."
United States
Anonymous traveler
$319 nightly
The price is $383
Mar 30 - Mar 31
Total with taxes and fees
Escape to wine country in your independent cottage in downtown Calistoga

Escape to Wine County in your independant Cottage in Downtown Calistoga

Escape to Wine County in your independant Cottage in Downtown Calistoga
Calistoga
9.6 out of 10, Exceptional, (34 reviews)
"Great getaway for a couple"
United States
David G.
$319 nightly
The price is $383
Mar 30 - Mar 31
Total with taxes and fees
Escape to Wine County in your independant Cottage in Downtown Calistoga

Glen Ellen Retreat #1 Hot Tub and King Beds

Glen Ellen Retreat #1 Hot Tub and King Beds
Glen Ellen
10.0 out of 10, Exceptional, (84 reviews)
"Great house in a perfect location. Short distance to Jack London State Park, various wineries, and walking distance to lovely restaurants near by. We enjoyed our long weekend and will definitely stay here again when we're up in the area!"
United States
sandra h.
$469 nightly
The price is $518
Mar 30 - Mar 31
Total with taxes and fees
Glen Ellen Retreat #1 Hot Tub and King Beds
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Windsor Hotel Reviews

Find out more about Windsor

Everything you need to know about Windsor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windsor vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Windsor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $90 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find vacation rentals in Windsor?

Yes, we have vacation rentals in Windsor near Dom Whitney Tasting Lounge, or you can go with a secluded option if you're looking for a relaxing stay. Our travelers say Windsor has a good selection of top-notch restaurants and wineries. Make sure you have time to check out the festivals while you're in the area.

What's the top vacation rental that Windsor has to offer?

Waterfront Home in Bodega Bay! 3Beds, 2Baths & panoramic ocean views.: Visitors like this Windsor vacation home rental. It is located on the beach and offers a patio, air-conditioning, and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Windsor?

Choose from 26 Expedia vacation rentals in Windsor for a memorable vacation.

What can I see and do in Windsor?

Family-friendly attractions include Dom Whitney Tasting Lounge and Powell's Sweet Shoppe - Windsor, whereas Russian River is a spot to enjoy the outdoors. Windsor Golf Club and Pacific Coast Air Museum are other places to visit while you're in town.

What are vacation rentals like in Windsor?

Vacation rentals are privately owned properties you can reserve for a few days or a quick weekend in Windsor. Vacation rentals offer amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can offer a sense of safety away from shared hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular choice for a small group gathering.